Sodium Azide → 2-Azido-6,7-diethylnaphthalene-1,4-dione

Participants

Reaction Steps

An aqueous solution of sodium azide (6.15 g; 0.095 mole) was added in one portion to a stirred, refluxing solution of 2-chloro-6,7-diethyl-1,4-naphthoquinone (18.0 g; 0.073 mole) in ethanol (180 ml) and the mixture refluxed for a further 2 mins. The red solution was cooled and the orange solid filtered off and washed with cold ethanol then water. After drying the product weighed 13.87 g (75%) and had m.p. 73°-76° C. (d). Recrystallisation from ethanol gave long orange needles of m.p. 74°-76° C. (d). (Found; C, 65.64; H, 5.27; N, 16.66; C14H13N3O2 requires; C, 65.87; H, 5.13; N, 16.46%).

Provenance & Evidence